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Journal articles on the topic 'Tetrahydropyrany'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Chen, Guangwu, Richard W. Franck, Guangli Yang, and Michael Blumenstein. "Anomeric effects of sulfones." Canadian Journal of Chemistry 80, no. 8 (2002): 894–99. http://dx.doi.org/10.1139/v02-095.

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The anomeric effect of the sulfone group in tetrahydropyrans has been determined. The value is >2 kcal mol1, which is larger than the A-value of a methyl group but less than the A-value of the sulfone in a tetrahydropyran. Hence, in an unsubstituted tetrahydropyranyl sulfone, the equatorial conformer predominates, whereas in a properly substituted methyltetrahydropyranyl sulfone, an axial sulfone is preferred over an axial methyl group.Key words: sulfone, tetrahydropyran, anomeric effect.

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2

di Dio, Philipp J., Stefan Zahn, Christian B. W. Stark, and Barbara Kirchner. "Understanding Selectivities in Ligand-free Oxidative Cyclizations of 1,5- and 1,6-Dienes with RuO4 from Density Functional Theory." Zeitschrift für Naturforschung B 65, no. 3 (2010): 367—s400. http://dx.doi.org/10.1515/znb-2010-0321.

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Quantum-chemical calculations using density functional theory were carried out to investigate the mechanism of the oxidative cyclization of 1,5- and 1,6-dienes with ruthenium tetroxide. Current experimental results show different selectivities for the formation of tetrahydrofuran and tetrahydropyran derivatives. Our theoretical data correctly reproduce the experimental selectivities. Transition structures for the first [3+2]-cycloaddition of RuO4 with ethene and for the second [3+2]- cycloaddition with two ethene molecules, 1,5-hexadiene, and 1,6-heptadiene were calculated. For the formation o

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3

Shouksmith, Andrew E., Laura E. Evans, Deborah A. Tweddle, et al. "Synthesis and Activity of Putative Small-Molecule Inhibitors of the F-Box Protein SKP2." Australian Journal of Chemistry 68, no. 4 (2015): 660. http://dx.doi.org/10.1071/ch14586.

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The tetrahydropyran 4-(((3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline was reported to disrupt the SCFSKP2 E3 ligase complex. Efficient syntheses of this tetrahydropyran derivative and analogues, including the des-dimethyl derivative 4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline, are described. The enantiomers of the des-dimethyl compound were obtained using Evans’ chiral auxiliaries. Structure–activity relationships for these tetrahydropyrans and analogues have been determined by measurement of growth-inhibitory ac

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4

Ryu, Jae-Sang, Yunjeong Park, and Jae Lee. "Synthesis of a Cyclic Analogue of Tuv N-Methyl Tubulysin." Synlett 26, no. 08 (2015): 1063–68. http://dx.doi.org/10.1055/s-0034-1379900.

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Tubulysins are the most potent antimitotic agents known so far. We are interested in the conformational effect of tubulysin and herein we report the design and synthesis of a conformationally rigid cyclic analogue of Tuv N-methyl tubulysin. A conformationally rigid tetrahydropyran moiety was incorporated into the Tuv fragment via enantioselective hetero Diels–Alder reaction to prevent the rotation of the Tuv chain. The following diastereoselective reductive amination yielded the (4-methylamino)tetrahydropyranyl Tuv fragment, which was coupled to d-Mep-l-Ile dipeptide fragment and Tup fragment

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5

Ouedraogo, Adama, and Jean Lessard. "The conformational behaviour of 2-aryloxytetrahydropyrans and 2-acetoxytetrahydropyran, and barrier to ring inversion." Canadian Journal of Chemistry 69, no. 3 (1991): 474–80. http://dx.doi.org/10.1139/v91-071.

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The 13C nuclear magnetic resonance data of a series of 2-(4-substituted-phenoxy)tetrahydropyrans at 156 K and in CF2Br2 and CHFCl2 solvents show that the axial preference increases with electron withdrawal in the aryloxy group: from 79% (ΔG°E→A = −0.4 kcal mol−1) (4-OCH3) to 90% (ΔG°E→A = −0.7 kcal mol−1) (4-NO2) in CF2Br2. The axial preference (anomeric effect) is smaller in the more polar CHFCl2 solvent, as expected, and the substituent effect is smaller also: change in ΔG°E→A from −0.3 (4-OCH3) to −0.5 (4-NO2) kcal mol−1. However, the axial preference of 2-acetoxytetrahydropyran is shown to

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6

Sipilä, Kaija, and Jarno Kansikas. "Structural Features of 2-S-Substituted Crystalline Tetrahydropyrans. Syntheses of 2-(2-Naphthylthiomethylthio)-Tetrahydropyran Derivatives." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 1 (2002): 19–31. http://dx.doi.org/10.1080/10426500210214.

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7

Díez-Poza, Carlos, Patricia Val, Francisco Pulido, and Asunción Barbero. "Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues." Marine Drugs 16, no. 11 (2018): 421. http://dx.doi.org/10.3390/md16110421.

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Tetrahydropyrans are abundantly found in marine natural products. The interesting biological properties of these compounds and their analogues make necessary the development of convenient procedures for their synthesis. In this paper, an atom economy access to tetrahydropyrans by intramolecular acid-mediated cyclization of silylated alkenols is described. p-TsOH has shown to be an efficient reagent to yield highly substituted tetrahydropyrans. Moreover, excellent diastereoselectivities are obtained both for unsubstituted and alkylsubstituted vinylsilyl alcohols. The methodology herein develope

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8

Clarke, Paul A., Philip B. Sellars, and Nadiah Mad Nasir. "A Maitland–Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones." Organic & Biomolecular Chemistry 13, no. 16 (2015): 4743–50. http://dx.doi.org/10.1039/c5ob00292c.

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New variations of the Maitland–Japp reaction have been developed to enable the synthesis of dihydropyrans and tetrahydropyrans with tertiary and quaternary stereocentres, including the functionalised tetrahydropyrans in Civet and the A-ring of lasonolide A.

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9

Dilworth, J. R., D. V. Griffiths, J. M. Hughes, and S. Morton. "SYNTHESIS OF 2-S-(2-TETRAHYDROPYRANYL)THIOETHYLPHOSPHINES RADICAL ADDITION OF PHOSPHINES TO AND 2-MERCAPTOETHYLPHOSPHINES BY FREE 2-(VINYLTHIO)TETRAHYDROPYRAN." Phosphorus, Sulfur, and Silicon and the Related Elements 71, no. 1-4 (1992): 249–51. http://dx.doi.org/10.1080/10426509208034518.

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10

Lee, Kiyoun, Hyoungsu Kim, and Jiyong Hong. "Stereoselective Synthesis of Tetrahydropyrans through Tandem and Organocatalytic Oxa-Michael Reactions: Synthesis of the Tetrahydropyran Cores of ent-(+)-Sorangicin A." European Journal of Organic Chemistry 2012, no. 5 (2011): 1025–32. http://dx.doi.org/10.1002/ejoc.201101549.

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11

Indusegaram, Sutharsiny, Andrew G. Katsifis, Damon D. Ridley, and Simone C. Vonwiller. "Nitrogen versus Oxygen Group Protection in Hydroxypropylbenzimidazoles." Australian Journal of Chemistry 56, no. 8 (2003): 819. http://dx.doi.org/10.1071/ch03012.

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In order to convert 1′H-benzimidazol-2′-ylpropanols into aryl ethers using Mitsunobu coupling, it was necessary to protect the benzimidazole nitrogen in the starting alcohols. Selective protection at nitrogen was achieved through N-benzyl derivatives, but attempts to protect the nitrogen directly through tert-butoxycarbonyl, acetyl, trityl, or tetrahydropyranyl derivatives were complicated either by selective reactions at oxygen or by the formation of bis-protected compounds. Transformations of some oxygen-protected derivatives are discussed, and in particular the conversion of the acetates of

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12

Katritzky, Alan R., Novruz G. Akhmedov, Sergey N. Denisenko, and Subbu Perumal. "An 1H and 13C NMR conformational study of 2-(benzotriazol-1-yl)-substituted tetrahydropyrans." Canadian Journal of Chemistry 79, no. 11 (2001): 1655–58. http://dx.doi.org/10.1139/v01-141.

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Proton and carbon NMR signals for 2-(benzotriazol-1-yl)tetrahydropyrans are assigned on the basis of spin decoupling, H,H-COSY, HETCOR, and nuclear Overhauser enhancement experiments. Conformational preferences are deduced. It was found that 2-(benzotriazol-1-yl) substituents: (i) prefer the equatorial orientation; and (ii) display a rotameric preference to minimize the electronic repulsion and (or) steric interaction.Key words: anomeric, NMR, tetrahydropyrans.

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13

Yates, Peter, and Françoise M. Winnik. "Bridged-ring steroids. III. The synthesis of bridged steroids with a bicyclo[2.2.1]heptane ring B system." Canadian Journal of Chemistry 63, no. 9 (1985): 2501–6. http://dx.doi.org/10.1139/v85-414.

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Reaction of cholesta-5,7-dien-3β-yl 2-tetrahydropyranyl ether with bromoform and potassium tert-butoxide gave 3′,3′-dibromo-3′,6β-dihydrocyclopropa[5,6]-5a-cholest-7-en-3β-yl 2-tetrahydropyranyl ether (1c), which on treatment with lithium aluminum hydride and water gave 5,8α-methano-5α-cholest-6-en-3β-yl 2-tetrahydropyranyl ether (2c). This has been converted to 3β-acetoxy-5,8α-methano-5α-cholestan-6-one (16c) and 3β-acetoxy-5,8α-methano-5α-cholestan-7-one (17c). A preliminary investigation of the photochemistry of 16c and 17c has shown that the incorporation of the bicyclo[2.2.1]heptan-2-one

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14

Iranpoor, Nasser, Habib Firouzabadi, and Mohammad Gholinejad. "4-Aminophenyldiphenylphosphinite (APDPP), a new heterogeneous and acid scavenger phosphinite — Conversion of alcohols, trimethylsilyl, and tetrahydropyranyl ethers to alkyl halides with halogens or N-halosuccinimides." Canadian Journal of Chemistry 84, no. 7 (2006): 1006–12. http://dx.doi.org/10.1139/v06-120.

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A new heterogeneous phosphinite, 4-aminophenyldiphenylphosphinite (APDPP), is prepared and used for the efficient conversion of alcohols, trimethylsilyl ethers, and tetrahydropyranyl ethers to their corresponding bromides, iodides, and chlorides in the presence of molecular halogens or N-halosuccinimides. The amino group in this phosphinite acts as an acid scavenger and removes the produced acid. A simple filtration easily removes the phosphinate by-product.Key words: 4-aminophenyldiphenylphosphinite, alcohol, trimethylsilyl ether, tetrahydropyranyl ether, alkyl halide.

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15

Bravo, R., M. Pintos, and A. Amigo. "Dependence upon temperature of the excess molar volumes of tetrahydropyran + n-alkane mixtures." Canadian Journal of Chemistry 73, no. 3 (1995): 375–79. http://dx.doi.org/10.1139/v95-049.

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Excess molar volumes VE, at 288.15 and 308.15 K and normal atmospheric pressure, are reported for the binary mixtures tetrahydropyran + n-alkanes (C7–C9). From the results, the differential coefficient (∂VE/∂T)p was estimated over the entire range of mole fractions. The Prigogine–Flory–Patterson theory and its applicability in predicting VE is tested. Keywords: Excess molar volumes, digital densimeter, tetrahydropyran, n-heptane, n-octane, n-nonane, Prigogine–Flory–Patterson theory.

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16

Fun, Hoong-Kun, Chin Wei Ooi, B. Palakshi Reddy, V. Vijayakumar, and S. Sarveswari. "10a-Hydroxy-9-(4-methoxyphenyl)-3,4,5,6,7,8a,9,10a-octahydro-1H-xanthene-1,8(2H)-dione." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2367—o2368. http://dx.doi.org/10.1107/s160053681203005x.

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In the title compound, C20H22O5, the tetrahydropyran, cyclohexene and cyclohexane rings of the xanthene ring system adopt half-chair, half-boat and chair conformations, respectively. The mean plane of the four roughly planar atoms of the tetrahydropyran ring (r.m.s. deviation = 0.111 Å) forms a dihedral angle of 82.91 (4)° with the methoxybenzene group. In the crystal, molecules are linkedviaO—H...O and C—H...O hydrogen bonds into sheets lying parallel to theacplane. The crystal is further consolidated by weak C—H...π interactions.

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17

Oates, R. P., and Paul B. Jones. "Photosensitized Tetrahydropyran Transfer." Journal of Organic Chemistry 73, no. 12 (2008): 4743–45. http://dx.doi.org/10.1021/jo800519h.

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18

Lu, Ran, Yangshan Li, Jiaqi Zhao, Jing Li, Shuguang Wang, and Lei Liu. "Redox deracemization of 1,3,4,9-tetrahydropyrano[3,4-b]indoles." Chemical Communications 54, no. 35 (2018): 4445–48. http://dx.doi.org/10.1039/c8cc01276h.

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19

Azzena, Ugo, Massimo Carraro, Gloria Modugno, Luisa Pisano, and Luigi Urtis. "Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents." Beilstein Journal of Organic Chemistry 14 (July 3, 2018): 1655–59. http://dx.doi.org/10.3762/bjoc.14.141.

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The application of heterogeneous catalysis and green solvents to the set up of widely employed reactions is a challenge in contemporary organic chemistry. We applied such an approach to the synthesis and further conversion of tetrahydropyranyl ethers, an important class of compounds widely employed in multistep syntheses. Several alcohols and phenols were almost quantitatively converted into the corresponding tetrahydropyranyl ethers in cyclopentyl methyl ether or 2-methyltetrahydrofuran employing NH4HSO4 supported on SiO2 as a recyclable acidic catalyst. Easy work up of the reaction mixtures

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20

Song, Jaeeun, L. Palanikumar, Yeongkyu Choi, et al. "The power of the ring: a pH-responsive hydrophobic epoxide monomer for superior micelle stability." Polymer Chemistry 8, no. 46 (2017): 7119–32. http://dx.doi.org/10.1039/c7py01613a.

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21

Ermanis, Kristaps, Yin-Ting Hsiao, Uğur Kaya, Alan Jeuken, and Paul A. Clarke. "The stereodivergent formation of 2,6-cis and 2,6-trans-tetrahydropyrans: experimental and computational investigation of the mechanism of a thioester oxy-Michael cyclization." Chemical Science 8, no. 1 (2017): 482–90. http://dx.doi.org/10.1039/c6sc03478k.

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22

Heravi, Majid M., Mahmood Tajbakhsh, and Mitra Ghassemzadeh. "Direct Oxidative Deprotection of Trimethylsilyl and Tetrahydropyranyl Ethers Using Alumina-Supported lodobenzene Diacetate under Non-Aqueous Conditions." Zeitschrift für Naturforschung B 54, no. 3 (1999): 394–96. http://dx.doi.org/10.1515/znb-1999-0318.

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23

Cui, Hai-Lei, Pandurang V. Chouthaiwale, Feng Yin, and Fujie Tanaka. "Catalytic asymmetric hetero-Diels–Alder reactions of enones with isatins to access functionalized spirooxindole tetrahydropyrans: scope, derivatization, and discovery of bioactives." Organic & Biomolecular Chemistry 14, no. 5 (2016): 1777–83. http://dx.doi.org/10.1039/c5ob02393a.

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24

Di Nicola, Francesco Paolo, Massimiliano Lanzi, Fabio Marchetti, Guido Pampaloni, and Stefano Zacchini. "Is bond stretch isomerism in mononuclear transition metal complexes a real issue? The misleading case of the MoCl5/tetrahydropyran reaction system." Dalton Transactions 44, no. 28 (2015): 12653–59. http://dx.doi.org/10.1039/c5dt01378j.

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25

Kozmon, Stanislav, and Igor Tvaroška. "DFT Study on 3-Substituted Tetrahydropyran-2-yl Radicals." Collection of Czechoslovak Chemical Communications 71, no. 10 (2006): 1453–69. http://dx.doi.org/10.1135/cccc20061453.

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A series of tetrahydropyran-2-yl radical (1) analogs was studied using density functional theory (DFT) to model conformational behavior of glycopyranosyl radicals. Calculations of the structure and stability of the 4C1, 1C4, B2,5, O,3B, and 4H3 ring conformers for tetrahydropyran-2-yl radical (1) and for 3-fluoro- (2, 7), 3-hydroxy- (3, 8), 3-methoxy- (4, 9), 3-acetoxy- (5, 10), and 3-(benzyloxy)tetrahydropyran-2-yl (6, 11) derivatives showed that conformational behavior of the 3-substituted radicals depends on both the electronic character and orientation of the C3 substituent. The calculatio

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26

Lin, Run, Hongnan Sun, Chao Yang, Wenbo Shen, and Wujiong Xia. "Visible light-induced difunctionalization of electron-enriched styrenes: synthesis of tetrahydrofurans and tetrahydropyrans." Chemical Communications 51, no. 2 (2015): 399–401. http://dx.doi.org/10.1039/c4cc08221d.

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27

Clarke, Paul A., Nadiah Mad Nasir, Philip B. Sellars, Alejandra M. Peter, Connor A. Lawson, and James L. Burroughs. "Synthesis of 2,6-trans- and 3,3,6-trisubstituted tetrahydropyran-4-ones from Maitland–Japp derived 2H-dihydropyran-4-ones: a total synthesis of diospongin B." Organic & Biomolecular Chemistry 14, no. 28 (2016): 6840–52. http://dx.doi.org/10.1039/c6ob01182a.

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28

Liu, Yi, and Ying-Yeung Yeung. "Ring strain-dictated divergent fluorinating Prins cyclization or semipinacol rearrangement." Organic & Biomolecular Chemistry 15, no. 31 (2017): 6478–82. http://dx.doi.org/10.1039/c7ob01567d.

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29

Sarkar, Sujit, Namita Devi, Bikoshita Porashar, Santu Ruidas, and Anil Saikia. "Stereoselective Synthesis of 4-O-Tosyltetrahydropyrans via Prins Cyclization Reaction of Enol Ethers." SynOpen 03, no. 01 (2019): 36–45. http://dx.doi.org/10.1055/s-0037-1611679.

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30

Matsubara, Hiroshi, Syouhei Suzuki, and Shun Hirano. "An ab initio and DFT study of the autoxidation of THF and THP." Organic & Biomolecular Chemistry 13, no. 16 (2015): 4686–92. http://dx.doi.org/10.1039/c5ob00012b.

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31

Hazarika, Nabajyoti, Barnali Sarmah, Manobjyoti Bordoloi, Prodeep Phukan, and Gakul Baishya. "Diastereoselective synthesis of tetrahydropyrans via Prins–Ritter and Prins–arylthiolation cyclization reactions." Organic & Biomolecular Chemistry 15, no. 9 (2017): 2003–12. http://dx.doi.org/10.1039/c6ob02692c.

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32

Mohammadi, Amir H., and Dominique Richon. "Equilibrium data of (tetrahydropyran+hydrogen sulphide) and (tetrahydropyran+methane) clathrate hydrates." Journal of Chemical Thermodynamics 48 (May 2012): 36–38. http://dx.doi.org/10.1016/j.jct.2011.12.038.

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33

Faustino, Hélio, Iván Varela, José L. Mascareñas, and Fernando López. "Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans." Chemical Science 6, no. 5 (2015): 2903–8. http://dx.doi.org/10.1039/c5sc00295h.

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34

Jiang, Yan, Shuo-Wen Yu, Yi Yang, et al. "Synthesis of polycyclic spirooxindoles via an asymmetric catalytic one-pot stepwise Aldol/chloroetherification/aromatization procedure." Organic & Biomolecular Chemistry 16, no. 36 (2018): 6647–51. http://dx.doi.org/10.1039/c8ob01713a.

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35

Movassagh, Barahman, and Salman Shokri. "An Efficient One-Pot Conversion of THP- and TMS Ethers to Sulfonate Esters Using FeCl3-Montmorillonite K-10 Clay." Zeitschrift für Naturforschung B 60, no. 7 (2005): 763–65. http://dx.doi.org/10.1515/znb-2005-0711.

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36

Ringstrand, Bryan, Martin Oltmanns, Jeffrey A. Batt, Aleksandra Jankowiak, Richard P. Denicola, and Piotr Kaszynski. "The preparation of 3-substituted-1,5-dibromopentanes as precursors to heteracyclohexanes." Beilstein Journal of Organic Chemistry 7 (March 31, 2011): 386–93. http://dx.doi.org/10.3762/bjoc.7.49.

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The methodology to prepare 3-substituted 1,5-dibromopentanes I and their immediate precursors, which include 3-substituted 1,5-pentanediols VII or 4-substituted tetrahydropyrans VIII, is surveyed. Such dibromides I are important intermediates in the preparation of liquid crystalline derivatives containing 6-membered heterocyclic rings. Four dibromides 1a–1d containing simple alkyl and more complex fragments at the 3-position were prepared. 3-Propyl- and 3-pentyl-pentane-1,5-diol (2a,b) were prepared starting from either glutaconate or malonate diesters, while tetrahydropyrans 3c and 3d were ob

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37

Gruet, Sébastien, Olivier Pirali, Amanda L. Steber, and Melanie Schnell. "The structural determination and skeletal ring modes of tetrahydropyran." Physical Chemistry Chemical Physics 21, no. 6 (2019): 3016–23. http://dx.doi.org/10.1039/c8cp06204h.

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38

Nasir, Nadiah Mad, Kristaps Ermanis, and Paul A. Clarke. "Strategies for the construction of tetrahydropyran rings in the synthesis of natural products." Org. Biomol. Chem. 12, no. 21 (2014): 3323–35. http://dx.doi.org/10.1039/c4ob00423j.

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39

Barbosa, Thaís M., Renan V. Viesser, Raymond J. Abraham, Roberto Rittner, and Cláudio F. Tormena. "Experimental and theoretical evaluation of trans-3-halo-2-hydroxy-tetrahydropyran conformational preferences. Beyond anomeric interaction." RSC Advances 5, no. 45 (2015): 35412–20. http://dx.doi.org/10.1039/c5ra04968g.

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40

Heravi, Majid M., Pegah Kazemian, Hossein A. Oskooie, and Mitra Ghassemzadeh. "HNO3/Silica Gel supported CAN; Oxidative Deprotection of Benzylic Tetrahydropyranyl Ethers under Solvent-free Conditions using Microwaves." Journal of Chemical Research 2005, no. 2 (2005): 105–6. http://dx.doi.org/10.3184/0308234054497128.

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Benzylic tetrahydropyranyl ethers are rapidly and selectively oxidised to the corresponding carbonyl compounds by HNO3/ silica gel supported cerium ammonium nitrate (CAN) under solvent free conditions using microwave.

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41

Badmus, Fatimat O., Joshua A. Malone, Frank R. Fronczek, and Rendy Kartika. "Correction: Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates." Chemical Communications 56, no. 45 (2020): 6154. http://dx.doi.org/10.1039/d0cc90228d.

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Correction for ‘Synthesis of functionalized tetrahydropyrans via cascade cycloaddition involving silyloxyallyl cation intermediates’ by Fatimat O. Badmus et al., Chem. Commun., 2020, 56, 5034–5037, DOI: 10.1039/D0CC01796E.

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42

Burt, Samuel P., Kevin J. Barnett, Daniel J. McClelland, et al. "Production of 1,6-hexanediol from tetrahydropyran-2-methanol by dehydration–hydration and hydrogenation." Green Chemistry 19, no. 5 (2017): 1390–98. http://dx.doi.org/10.1039/c6gc03606f.

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43

Chopra, Reenu, Ning Shan, W. D. Sam Motherwell, and William Jones. "2-(p-Nitrophenoxy)tetrahydropyran." Acta Crystallographica Section E Structure Reports Online 60, no. 11 (2004): o1923—o1924. http://dx.doi.org/10.1107/s1600536804023748.

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44

Padhi, Birakishore, D. Srinivas Reddy, and Debendra K. Mohapatra. "Gold-catalyzed diastereoselective synthesis of 2,6-trans-disubstituted tetrahydropyran derivatives: application for the synthesis of the C1–C13 fragment of bistramide A and B." RSC Advances 5, no. 117 (2015): 96758–68. http://dx.doi.org/10.1039/c5ra17646h.

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An efficient Au(iii)-catalyzed diastereoselective allylation leading to 2,6-trans-disubstituted tetrahydropyrans and application for the synthesis of the C1–C13 fragment of bistramide A and B is described.

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45

Nakate, Ashwini K., Madhukar S. Pratapure, and Ravindar Kontham. "Bismuth(iii)-catalyzed cycloisomerization and (hetero)arylation of alkynols: simple access to 2-(hetero)aryl tetrahydrofurans and tetrahydropyrans." Organic & Biomolecular Chemistry 16, no. 17 (2018): 3229–40. http://dx.doi.org/10.1039/c8ob00368h.

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2-(Hetero)aryl tetrahydrofurans and tetrahydropyrans were successfully synthesized using Bi(OTf)<sub>3</sub>-catalyzed hydroalkoxylation (cycloisomerization) of alkynols (via 5 or 6 exo-dig cyclization) and intermolecular (hetero)arylation.

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46

Koch, Alexander, Sven Krieck, Helmar Görls, and Matthias Westerhausen. "5-Methyl-2-thienylcalcium iodide." Dalton Transactions 47, no. 36 (2018): 12534–39. http://dx.doi.org/10.1039/c8dt01398e.

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47

Pathe, Gulab Khushalrao, and Naseem Ahmed. "SeO2 in water: a mild and efficient promoter for deprotection of acetyl, methoxymethyl and tetrahydropyranyl ethers and sequel oxidation of methyl/methylene carbons of alpha carbonyl carbon." RSC Advances 5, no. 73 (2015): 59114–19. http://dx.doi.org/10.1039/c5ra09986b.

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SeO<sub>2</sub> in water is found as mild and efficient promoter for the deprotection of acetyl, tetrahydropyranyl, methoxymethyl ethers and sequel oxidation of methyl/methylene carbons of alpha carbonyl carbon.

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48

Bharath, Yada, Utkal Mani Choudhury, N. Sadhana, and Debendra K. Mohapatra. "The Mukaiyama type aldol reaction for the synthesis of trans-2,6-disubstituted tetrahydropyrans: synthesis of diospongin A and B." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9169–81. http://dx.doi.org/10.1039/c9ob01549c.

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The synthesis of 2,6-trans-disubstituted tetrahydropyrans following the Mukaiyama type aldol reaction through C–C bond formation demonstrates the practicality of this protocol in the total synthesis of diospongin A and B.

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49

Lambert, Lester J., Marvin J. Miller, and Paul W. Huber. "Tetrahydrofuranyl and tetrahydropyranyl protection of amino acid side-chains enables synthesis of a hydroxamate-containing aminoacylated tRNA." Organic & Biomolecular Chemistry 13, no. 8 (2015): 2341–49. http://dx.doi.org/10.1039/c4ob02212b.

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O-protection using tetrahydrofuranyl or tetrahydropyranyl enabled addition of a hydroxamate-containing unnatural amino acid to a suppressor tRNA, allowing subsequent site-specific incorporation of the amino acid into the transcription factor, TFIIIA.

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50

Mihai, Gheorghe, and Teodor-Silviu Balaban. "Catalytic Hydrogenation of Pyrylium Salts: A Convenient Route to Alkyl-Substituted Tetrahydropyrans." Zeitschrift für Naturforschung B 41, no. 4 (1986): 502–4. http://dx.doi.org/10.1515/znb-1986-0417.

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2,4.6-Trialkylpyrylium perchlorates afford in high yields by hydrogenation on palladium catalyst at room tem perature the corresponding all-dis-2,4.6-trialkyltetrahydropyrans, whereas other reaction conditions lead to mixtures of tetrahydropyrans and hydrogenolyzed products

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